Triethylamine → (S)-2-(2-Methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 736655Notes

Reaction equation

HRID 736655 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][CH2:15][OH:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][CH2:15][O:16][S:18]([CH3:17])(=[O:20])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1514243(S)-1-N-Boc-piperidine-2-ethanol

Product 1

HCID 57850304(S)-2-(2-Methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (0.300 g, 1.30 mmol) in dichloromethane (5 mL) was added methane sulfonylchloride 0.304 mL, 3.9 mmol) and triethylamine (0.547 mL, 3.9 mmol) at rt for 1-16 h. The reaction mixture was diluted with dichloromethane and washed with NaHCO3 (10%, W/V), followed by water. The dichloromethane layer was dried (Na2SO4), filtered and the solvent was evaporated to dryness. The product was sufficiently pure for the next step and was used without any further purification. LC-MS [M+Na] 329.9

Workup

  1. washwashed with NaHCO3 (10%, W/V)
  2. dry with materialThe dichloromethane layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated to dryness
  5. customwas used without any further purification

Sources & evidence

ORD record
ord-5ee32051df284ed5bab41a1eafd09b0a
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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